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EP0093949B1 - Azacycloheptan-2-ones sulfinyliques et sulfonyliques, procédé pour leur préparation et leur application comme suppléments pour la pâture - Google Patents

Azacycloheptan-2-ones sulfinyliques et sulfonyliques, procédé pour leur préparation et leur application comme suppléments pour la pâture Download PDF

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Publication number
EP0093949B1
EP0093949B1 EP83104096A EP83104096A EP0093949B1 EP 0093949 B1 EP0093949 B1 EP 0093949B1 EP 83104096 A EP83104096 A EP 83104096A EP 83104096 A EP83104096 A EP 83104096A EP 0093949 B1 EP0093949 B1 EP 0093949B1
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EP
European Patent Office
Prior art keywords
azacycloheptan
optionally substituted
sulfinyl
alkyl
sulfonyl
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Expired
Application number
EP83104096A
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German (de)
English (en)
Other versions
EP0093949A1 (fr
Inventor
Gerd Dr. Fengler
Artur Dr. Botta
Martin Dr. Scheer
Friedrich Dr. Berschauer
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D223/08—Oxygen atoms
    • C07D223/10—Oxygen atoms attached in position 2
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/116—Heterocyclic compounds
    • A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism

Definitions

  • the invention relates to new sulfinyl and sulfonylazacycloheptan-2-ones, processes for their preparation and their use as agents for promoting the growth and feed conversion in animals.
  • Sulfinyl- and sulfonyl azacycloheptan-2-ones of the general formula (Ia) are particularly preferred in which n and R 2 have the meaning given above and the sulfinyl or sulfonyl radical is in the a or ⁇ position.
  • the sulfinyl- and sulfonylazacycloheptan-2-ones according to the invention show a surprisingly pronounced nutritional effect which has not yet been found in compounds of this class of substance, moreover they are neither mutagenic (Ames test) nor estrogenically active and thus provide an enrichment of technology.
  • the optionally substituted C 1-4 alkyl R and R 3 are straight-chain or branched alkyl radicals having up to 4 carbon atoms. Substituted methyl, ethyl, n- and i-propyl, n-, i- and t-butyl may be mentioned as examples.
  • Alkylcarbomyl R stands for carbamoyl radicals with up to 4, in particular up to 2, carbon atoms in the alkyl part, for example methyl- and ethylcarbamoyl.
  • Substituted alkyl R 2 represents straight-chain or branched alkyl having 1 -18, preferably 1-12 carbon atoms. Substituted methyl, ethyl, n- and i-propyl, n-, i- and t-butyl, pentyl, hexyl, dodecyl may be mentioned as examples.
  • Possible optionally substituted alkenyl radicals R 2 are straight-chain or branched alkenyl radicals having up to 6, preferably up to 4, carbon atoms. Examples include: ethenyl, propenyl- (1), propenyl- (2), butenyl- (3).
  • Substituted cycloalkyl R 2 is mono-, biodertricyclic and preferably contains 3 to 10, in particular 3 to 7, carbon atoms.
  • Substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, cycloheptyl, bicyclo- [2,2,1] -heptyl and adamantyl may be mentioned as examples.
  • the optionally substituted aralkyl R z is optionally substituted aralkyl in the aryl part and / or alkyl part with preferably 6 or 10, in particular 6 carbon atoms in the aryl part and preferably 1 to 4, in particular 1 or 2 carbon atoms in the alkyl part, the alkyl part being straight-chain or branched can.
  • Exemplified are optionally substituted benzyl and phenylethyl.
  • Optionally substituted aryl R 2 is aryl with preferably 6 to 10 carbon atoms in the aryl part.
  • Substituted phenyl or naphthyl may be mentioned as examples.
  • Substituents in the phenyl ring are in the o, m or p position.
  • heterocyclyl R 2 are heteroparaffinic, heteroaromatic or heteroolefinic 5- to 7-membered, preferably 5 or 6-membered rings with preferably 1 to 3, in particular 1 or 2 identical or different heteroatoms.
  • the heteroatoms are oxygen, sulfur or nitrogen.
  • Examples that may be substituted are thienyl, furyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrrolyl, imidazolyl, pyrazolyl, oxdiazolyl, thiatriazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, tetrahydrofuranyl, and dioxanyl, pyridine, pyrolidyl, pyridine, pyridine, pyridlyl, pyridlyl, pyridlyl, pyridlyl, pyridlyl, pyridlyl, pyridlyl, pyridyl, pyridyl, pyridyl, pyridyl, pyridyl, pyridyl, pyridyl, pyridyl, pyridyl
  • heterocyclic rings it is also possible for the heterocyclic rings to be fused to one or more residues from the benzene series.
  • Substituted alkyl, alkenyl, cycloalkyl, aralkyl, aryl and heterocyclyl radicals can carry one or more, preferably 1 to 3, in particular 1 or 2 identical or different radicals R 4 , where R 4 is straight-chain or branched alkyl, preferably 1 to 6, especially 1 to 4 carbon atoms, e.g. B. methyl, ethyl, n- and i-propyl, n-, i- and t-butyl and CF 3 , CCI 3 and for aryl, z. B. phenyl, CH 3 0-, C 2 H 5 O- and for aryloxy, z. B.
  • oxidizing agents which can be used according to the invention are also known, examples being hydrogen peroxide, performic acid, peracetic acid, perbenzoic acid, m-chloroperbenzoic acid, sodium metaperiodate and atmospheric oxygen. Further suitable oxidizing agents can be found in C. Ferri, " Reactions of Organic Synthesis” (G. Thieme Verlag, Stuttgart 1978, p. 470).
  • inert organic solvents are suitable as diluents. These preferably include chlorinated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,2,2-trichloroethane and chlorobenzene, alcohols, preferably methanol, ethanol and isopropanol, lower fatty acids, preferably formic acid, acetic acid and propionic acid and water.
  • chlorinated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,2,2-trichloroethane and chlorobenzene
  • alcohols preferably methanol, ethanol and isopropanol
  • lower fatty acids preferably formic acid, acetic acid and propionic acid and water.
  • the reaction temperatures can be varied over a wide range. In general, between about -20 and about + 100 ° C, preferably between 0 and + 60 ° C.
  • the reaction can be carried out under normal pressure, but also under reduced and elevated pressure. Generally one works at normal pressure.
  • reaction batches for isolating the compounds according to the invention are worked up in a generally known manner.
  • X represents halogen, preferably chlorine, bromine and iodine, in particular chlorine and bromine.
  • R has the meaning given above.
  • R 2 has the meaning given above, M
  • M stands for an alkali application, preferably for the sodium or potassium cation.
  • alkali sulfinates which can be used according to the invention are known (Houben-Weyl, G. Thieme Verlag, Stuttgart, 1955, Vol. IX, pp. 289-342).
  • inert organic solvents are suitable as diluents. These preferably include alcohol such as methanol, ethanol and isopropanol, ethers such as dioxane or tetrahydrofuran, dipolar aprotic solvents such as dimethyl sulfoxide, dimethylformamide and N-methylpyrrolidone and water.
  • alcohol such as methanol, ethanol and isopropanol
  • ethers such as dioxane or tetrahydrofuran
  • dipolar aprotic solvents such as dimethyl sulfoxide, dimethylformamide and N-methylpyrrolidone and water.
  • the process according to the invention can be carried out in the presence of only one or more solvents or water and one or more water-immiscible solvents.
  • the reaction temperatures can be varied over a wide range. In general, one works between about 0 and +250, preferably between +50 and + 190 ° C.
  • the reaction can be carried out under normal pressure, but also under reduced and increased pressure. Generally one works at normal pressure.
  • the starting materials are used in equimolar amounts, but it may be expedient to use the alkali metal sulfinate of the general formula (V) in excess in order to increase the reaction rate.
  • reaction batches for isolating the compounds according to the invention are worked up in a generally known manner.
  • the azacycloheptan-2-one of the formula (I) according to the invention surprisingly have the property of promoting and accelerating the growth in animals, so that these compounds can be used in all areas of animal breeding and animal husbandry for the purposes mentioned.
  • the effectiveness of the compounds used according to the invention is largely independent of the type and sex of the animals.
  • the azacycloheptan-2-ones of the formula (I) according to the invention have proven particularly valuable in the rearing and keeping of young and fattening animals.
  • farm animals and ornamental animals may be mentioned as examples of animals in which the compound can be used to promote and accelerate growth:
  • Warm-blooded animals such as cattle, pigs, horses, sheep, goats, cats, dogs, rabbits, fur animals, e.g. B. mink and chinchilla, poultry, z. B. chickens, geese, ducks, turkeys, broilers, pigeons, parrots and canaries and cold-blooded animals, such as fish, e.g. B. carp and reptiles, e.g. B. snakes.
  • Azacycloheptane-2-ones of the formula (I) are preferably used in the rearing and keeping of ruminants such as calves, goats, sheep and also in pigs and chicks.
  • the amount of azacycloheptan-2-ones of formula (I), which is administered to the animals to achieve the desired effect, can be varied widely. It is preferably about 0.5 to 500, in particular 1 to 100 mg / kg body weight / d.
  • the duration of administration can. from a few hours or days to several years. The appropriate amount of active ingredient and the appropriate duration of administration depend in particular on the type, age, gender, health status and type of keeping of the animals and are easy to determine by any person skilled in the art.
  • the compounds are administered to the animals by the customary methods.
  • the mode of administration depends in particular on the type, behavior and state of health of the animals.
  • the administration can take place orally or parenterally once or several times a day at regular or irregular intervals.
  • oral administration is preferred in most cases, in particular in the rhythm of the animals' food and / or drink intake.
  • the compounds can be administered as pure substances or in formulated form, that is to say in a mixture with non-toxic inert carriers, as such solid, semisolid or liquid diluents, fillers and formulation auxiliaries of all types are to be understood.
  • Azacycloheptan-2-ones of the formula (1) can, if appropriate, also be administered in a suitable form in a suitable form together with pharmaceutical active ingredients, mineral salts, trace elements, vitamins, protein substances, fats, colorants and / or flavorings.
  • Oral administration together with the feed and / or drinking water is recommended, the active ingredients being added to the total amount or only parts of the feed and / or drinking water as required.
  • the compounds can be added to the feed and / or drinking water by conventional methods by simple mixing as pure substances, preferably in finely divided form or in formulated form in a mixture with edible non-toxic carriers, optionally also in the form of a premix or a feed concentrate.
  • the feed and / or drinking water can, for example, contain the active ingredient according to the invention in a concentration of about 5 to 500, in particular 5 to 100 ppm.
  • the optimum level of the concentration of the active ingredient in the feed and / or drinking water depends in particular on the amount of feed and / or drinking water intake by the animals and can be easily determined by any person skilled in the art.
  • the type of feed and its composition are irrelevant. All customary, commercially available or special feed compositions can be used which preferably contain the usual balance of energy and building materials including vitamins and minerals necessary for a balanced diet.
  • the feed can be composed, for example, of vegetable substances, e.g. B. hay, beets, cereals, cereal by-products, animal substances, e.g. As meat, fats, bone meal, fish products, vitamins, for. B. Vitamin A, D complex and B complex, proteins, amino acids, e.g. B. DL-methionine and inorganic substances, e.g. B. lime and table salt.
  • Feed concentrates contain azacycloheptan-2-one of the formula (I) in addition to edible substances, e.g. B. rye flour, corn flour, soybean flour or lime, possibly with other nutrients and builders as well as proteins, mineral salts and vitamins. They can be produced using the usual mixing methods.
  • the active ingredients may also be suitable agents covering their surface, e.g. B. with non-toxic waxes or gelatin from air, light and / or moisture.
  • the active ingredient premix contains azacycloheptan-2-one of the formula (I) in the desired amount, for. B. 100 mg and an additional 1 g of DL-methionine and so much soybean meal that 2.5 g of premix arise.
  • the feed mixtures specified are preferably for rearing and fattening chicks or

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Food Science & Technology (AREA)
  • Zoology (AREA)
  • Animal Husbandry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Obesity (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Fodder In General (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
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Claims (10)

1. Sulfinyl-etsulfonylazacycloheptane-2-ones de formule générale (1):
Figure imgb0038
dans laquelle
n = 1 ou 2,
R1 représente H, un groupe alkyle en C1-C4 éventuellement substitué, phényle éventuellement substitué, acétyle, propionyle, benzoyle et (alkyle en C1-C4)-carbamoyle,
R2 représente un groupe alkyle en C1-C18 éventuellement substitué, alcényle en C2-C6 éventuel- lementsubstitué, cycloalkyle en C3-C10 éventuellement substitué, aralkyle contenant 6 ou 10 atomes de carbone dans la partie aryle et 1 à 4 atomes de carbone dans la partie alkyle, éventuellement substitué, aryle en C6-C10 éventuellement substitué ou un reste hétérocyclique contenant 5 à 7 atomes cycliques et 1 à 3 hétéroatomes identiques ou différents, éventuellement substitué, le reste sulfinyle ou sulfonyle pouvant se trouver dans la position α à δ,
R3 représente H ou un groupe alkyle en C1-C4 et peut occuper la position a à s.
Les restes alkyle, alcényle, cycloalkyle, aralkyle, aryle et les restes hétérocycliques éventuellement substitués peuvent porter un ou plusieurs restes R4 identiques ou différents, R4 représentant un groupe alkyle droit ou ramifié en C1-C6 et CF3, CCl3 ou encore phényle, CH3O, C2H5O ou encore phénoxy, ou bien CH3S, C2H5S, HCO-NH-, diméthylamino, diéthylamino, CH3OCO-, C2H5OCO-, un halogène, un groupe -C=N, COOH, -NH2 ou encore NO2.
2. Sulfinyl-etsulfonylazacycloheptane-2-ones selon la revendication 1, caractérisées en ce qu'elles répondent à la formule générale (la)
Figure imgb0039
dans laquelle
n et R2 ont les significations indiquées dans la revendication 1 et le reste sulfinyle ou sulfonyle se trouve en position a ou β.
3. La 3-[(4-chlorophényl)sulfinyl]azacyclo- heptane-2-one.
4. La 4-[(4-chlorophényl)sulfinyl]azacyclo- heptane-2-one.
5. La 4-[(4-méthylphényl)sulfonyl]azacyclo- heptane-2-one. 6. Procédé de préparation des sulfinyl- et sul- fonylazacycloheptane-2-ones de formule générale (I):
Figure imgb0040
dans laquelle
n = 1 ou 2,
R1 représente H, un groupe alkyle en C1-C4 éventuellement substitué, phényle éventuellement substitué, acétyle, propionyle, benzoyle et (alkyle en C1-C4)-carbamoyle,
R2 représente un groupe alkyle en C1-C18 éventuellement substitué, alcényle en C2-C6 éventuel- lementsubstitué, cycloalkyleen C3-C10 éventuellement substitué, aralkyle contenant 6 ou 10 atomes de carbone dans la partie aryle et 1 à 4 atomes de carbone dans la partie alkyle, éventuellement substitué, aryle en C6-C10 éventuellement substitué ou un reste hétérocyclique contenant 5 à 7 atomes cycliques et 1 à 3 hétéroatomes identiques ou différents, éventuellement substitué, le reste sulfinyle ou sulfonyle pouvant se trouver dans la position α à δ,
R3 représente H ou un groupe alkyle en C1-C4 et peut occuper la position a à s;

les restes alkyle, alcényle, cycloalkyle, aralkyle, aryle et les restes hétérocycliques éventuellement substitués peuvent porter un ou plusieurs restes R4 identiques ou différents, R4 représentant un groupe alkyle droit ou ramifié en C1-C6 et CH3, CCl3 ou encore phényle, CH3O, C2H5O ou encore phénoxy, ou encore CH3S, C2H5S, HCO-NH-, diméthylamino, diéthylamino, CH3OCO-, C2H5OCO-, un halogène, un groupe -C=N, COOH et -NH2 ou NO2, caractérisé en ce que l'on fait réagir des thioéthers de formule (II) :
Figure imgb0041
dans laquelle
R1, R2 et R3 ont les significations indiquées ci- dessus et le reste sulfényle peut se trouver en position a à 8, avec des agents oxydants appropriés, éventuellement en présence de solvants inertes.
7. Procédé de préparation des 3-sulfonylazacy- cloheptane-2-ones de formule (III):
Figure imgb0042
dans laquelle
R1 et R2 ont les significations indiquées dans la revendication 1, caractérisé en ce que l'on fait réagir des 3-halogénoazacycloheptane-2-ones de formule (IV):
Figure imgb0043
dans laquelle
R, a les significations indiquées dans la revendication 1 et X représente un halogène, avec des sul- finates de formule (V) :
Figure imgb0044
dans laquelle
R2 a les significations indiquées dans la revendication 1 et M⊕ représente un cation de métal alcalin, éventuellement en présence de solvants inertes.
8. Additif pour l'alimentation animale, contenant des sulfinyl- et sulfonylazacycloheptane-2- ones de formule (I) de la revendication 1.
9. Prémélanges pour la préparation d'aliments pour animaux, contenant des sulfinyl- et sulfonyl- azacycloheptane-2-ones de formule (I) de la revendication 1.
10. Utilisation des sulfinyl- et sulfonylazacy- cloheptane-2-ones de formule (I) de la revendication 1 dans des additifs à l'alimentation animale et des prémélanges pour la préparation d'aliments pour animaux.
EP83104096A 1982-05-08 1983-04-27 Azacycloheptan-2-ones sulfinyliques et sulfonyliques, procédé pour leur préparation et leur application comme suppléments pour la pâture Expired EP0093949B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT83104096T ATE18553T1 (de) 1982-05-08 1983-04-27 Sulfinyl- und sulfonyl-azacycloheptan-2-one, verfahren zu ihrer herstellung sowie ihre verwendung als futterzusatzstoffe.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19823217373 DE3217373A1 (de) 1982-05-08 1982-05-08 Sulfinyl- und sulfonyl-azacycloheptan-2-one, verfahren zu ihrer herstellung sowie ihre verwendung als futterzusatzstoffe
DE3217373 1982-05-08

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EP0093949A1 EP0093949A1 (fr) 1983-11-16
EP0093949B1 true EP0093949B1 (fr) 1986-03-12

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US (1) US4468392A (fr)
EP (1) EP0093949B1 (fr)
JP (1) JPS58208274A (fr)
KR (1) KR840004727A (fr)
AR (1) AR231837A1 (fr)
AT (1) ATE18553T1 (fr)
AU (1) AU1416683A (fr)
BR (1) BR8302389A (fr)
CS (1) CS240961B2 (fr)
DE (2) DE3217373A1 (fr)
DK (1) DK204883A (fr)
ES (1) ES8402579A1 (fr)
FI (1) FI831549L (fr)
GR (1) GR78556B (fr)
HU (1) HU191833B (fr)
NZ (1) NZ204136A (fr)
PH (1) PH20414A (fr)
PL (1) PL241836A1 (fr)
ZA (1) ZA833234B (fr)

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US5635103A (en) * 1995-01-20 1997-06-03 The Procter & Gamble Company Bleaching compositions and additives comprising bleach activators having alpha-modified lactam leaving-groups
US20040074053A1 (en) * 2002-10-16 2004-04-22 Kimberly-Clark Worldwide, Inc. Apparatus and method for forming a layer of blended fibers into a continuous web
GB2418425B (en) 2004-08-11 2008-09-03 Univ Cambridge Tech Anti-inflammatory agents

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EP0049505A3 (fr) * 1980-10-06 1982-08-04 Merck & Co. Inc. Dérivés substitués de caprolactames, procédé pour leur préparation, et composition pharmaceutique les contenant, ainsi que les intermédiaires

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US4468392A (en) 1984-08-28
ATE18553T1 (de) 1986-03-15
EP0093949A1 (fr) 1983-11-16
PH20414A (en) 1987-01-05
FI831549L (fi) 1983-11-09
AR231837A1 (es) 1985-03-29
AU1416683A (en) 1983-11-10
BR8302389A (pt) 1984-01-10
DE3362507D1 (en) 1986-04-17
ZA833234B (en) 1984-08-29
ES522166A0 (es) 1984-02-01
JPS58208274A (ja) 1983-12-03
DE3217373A1 (de) 1983-11-10
CS240961B2 (en) 1986-03-13
DK204883D0 (da) 1983-05-06
DK204883A (da) 1983-11-09
PL241836A1 (en) 1986-02-11
NZ204136A (en) 1985-05-31
FI831549A0 (fi) 1983-05-05
ES8402579A1 (es) 1984-02-01
GR78556B (fr) 1984-09-27
CS314683A2 (en) 1985-06-13
KR840004727A (ko) 1984-10-24
HU191833B (en) 1987-04-28

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